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Volume 69 
Part 12 
Page o1763  
December 2013  

Received 5 November 2013
Accepted 7 November 2013
Online 13 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 13.1
Details
Open access

5-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth­yl]-5H-dibenzo[b,f]azepine

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title compound, C24H20N4, the azepine ring adopts a boat conformation. The dihedral angle between the benzene rings fused to the azepine ring is 49.40 (9)°. The triazole ring makes a dihedral angle of 77.88 (9)° with the terminal phenyl ring. In the crystal, mol­ecules are linked via C-H...[pi] inter­actions and a parallel slipped [pi]-[pi] inter­action [centroid-centroid distance = 3.7324 (9), normal distance = 3.4060 (6) and slippage = 1.526 Å], forming a three-dimensional network.

Related literature

For the use of dibenzo azepine derivatives in the preparation of carbamazepine, see: Rockliff & Davis (1966[Rockliff, B. W. & Davis, E. H. (1966). Arch. Neurol. 15, 129-136.]). For their anti­tumor properties, see: Al-Qawasmeh et al. (2009[Al-Qawasmeh, R. A., Lee, Y., Cao, M.-Y., Gu, X., Viau, S., Lightfoot, J., Wright, J. A. & Young, A. H. (2009). Bioorg. Med. Chem., 19 104-107.]). For related structures, see: Abdoh et al. (2013[Abdoh, M. M. M., Madan Kumar, S., Vinay Kumar, K. S., Manjunath, B. C., Sadashiva, M. P. & Lokanath, N. K. (2013). Acta Cryst. E69, o17.]); Manjunath et al. (2013[Manjunath, B. C., Vinay Kumar, K. S., Madan Kumar, S., Sadashiva, M. P. & Lokanath, N. K. (2013). Acta Cryst. E69, o1233.]). For ring-puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20N4

  • Mr = 364.44

  • Monoclinic, P 21 /c

  • a = 11.4339 (10) Å

  • b = 11.7140 (12) Å

  • c = 14.4527 (13) Å

  • [beta] = 98.610 (4)°

  • V = 1913.9 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.60 mm-1

  • T = 296 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.871, Tmax = 0.882

  • 11434 measured reflections

  • 3160 independent reflections

  • 2742 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.135

  • S = 1.06

  • 3160 reflections

  • 242 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C9-C14 rings, respectively

D-H...A D-H H...A D...A D-H...A
C18-H18A...Cg2i 0.97 2.83 3.600 (2) 137
C20-H20...Cg1i 0.93 2.79 3.642 (2) 153
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2664 ).


Acknowledgements

We are grateful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility.

References

Abdoh, M. M. M., Madan Kumar, S., Vinay Kumar, K. S., Manjunath, B. C., Sadashiva, M. P. & Lokanath, N. K. (2013). Acta Cryst. E69, o17.  [CSD] [CrossRef] [IUCr Journals]
Al-Qawasmeh, R. A., Lee, Y., Cao, M.-Y., Gu, X., Viau, S., Lightfoot, J., Wright, J. A. & Young, A. H. (2009). Bioorg. Med. Chem., 19 104-107.
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Manjunath, B. C., Vinay Kumar, K. S., Madan Kumar, S., Sadashiva, M. P. & Lokanath, N. K. (2013). Acta Cryst. E69, o1233.  [CSD] [CrossRef] [IUCr Journals]
Rockliff, B. W. & Davis, E. H. (1966). Arch. Neurol. 15, 129-136.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1763  [ doi:10.1107/S1600536813030547 ]

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